30 days in Kentucky Itinerary

30 days in Kentucky Itinerary

Created using Inspirock Kentucky tour planner

Make it your trip
Drive
1
Lexington
— 8 nights
Drive
2
Louisville
— 8 nights
Drive
3
Cave City
— 6 nights
Drive
4
Hopkinsville
— 3 nights
Drive
5
Paducah
— 4 nights
Fly

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Lexington

— 8 nights

Horse Capital of the World

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
You'll explore the less-touristy side of things at Mary Todd Lincoln House and The Great American Dollhouse Museum. Change things up with these side-trips from Lexington: Shaker Village of Pleasant Hill (in Harrodsburg), Red River Gorge Geological Area (in Winchester) and Natural Bridge State Resort Park (in Slade). The adventure continues: learn insider's secrets on a distillery tour, look for all kinds of wild species at Unique Horse Farm Tours, don't miss a visit to Daniel Boone's Grave, and go for a walk through Kentucky Bourbon Trail.

To see traveler tips, more things to do, maps, and tourist information, read our Lexington itinerary planner.

Columbus to Lexington is an approximately 3-hour car ride. You can also take a bus; or fly. Expect a daytime high around 56°F in November, and nighttime lows around 36°F. Finish your sightseeing early on the 9th (Tue) to allow enough time to drive to Louisville.

Things to do in Lexington

Historic Sites · Breweries & Distilleries · Museums · Parks

Side Trips

Louisville

— 8 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Step off the beaten path and head to Conrad-Caldwell House Museum (Conrad's Castle) and Kentucky Peerless Distilling Co. Venture out of the city with trips to Bardstown (Old Bardstown Village Civil War Museum, Willett Distilling Company, &more) and Bernheim Arboretum & Forest (in Clermont). Next up on the itinerary: stroll around Cherokee Park, get thoroughly spooked out with a ghost and vampire tour, see the interesting displays at Frazier History Museum, and explore the different monuments and memorials at Cave Hill Cemetery.

Planning Louisville trip won't be overwhelming when you use Inspirock's itinerary maker.

Drive from Lexington to Louisville in 1.5 hours. Alternatively, you can take a bus. In November, daytime highs in Louisville are 57°F, while nighttime lows are 37°F. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Cave City.

Things to do in Louisville

Breweries & Distilleries · Parks · Museums · Historic Sites

Side Trips

Cave City

— 6 nights
Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
You'll explore the less-touristy side of things at Limestone Branch Distillery and Swope's Cars of Yesteryear Museum. Venture out of the city with trips to Freeman Lake Park (in Elizabethtown), Abraham Lincoln Birthplace National Historical Park (in Hodgenville) and Cub Run Cave (in Cub Run). And it doesn't end there: surround yourself with nature on a nature and wildlife tour, Head underground at Diamond Caverns, admire nature's wide array of creatures at Kentucky Down Under Adventure Zoo, and see the interesting displays at Dinosaur World.

To find photos, other places to visit, traveler tips, and more tourist information, read our Cave City sightseeing planning website.

Traveling by car from Louisville to Cave City takes 1.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of bus and taxi. Due to the time zone difference, you'll gain 1 hour traveling from Louisville to Cave City. In November, daily temperatures in Cave City can reach 57°F, while at night they dip to 36°F. Finish your sightseeing early on the 23rd (Tue) so you can travel to Hopkinsville.

Things to do in Cave City

Parks · Nature · Museums · Outdoors

Side Trips

Hopkinsville

— 3 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. You'll explore the less-touristy side of things at Casey Jones Distillery and Jefferson Davis State Historic Site. You'll find plenty of places to visit near Hopkinsville: Woodlands Nature Station (in Cadiz), Smothers Park (in Owensboro) and Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium (in Golden Pond).

To find more things to do, traveler tips, photos, and more tourist information, use the Hopkinsville trip itinerary maker.

Traveling by car from Cave City to Hopkinsville takes 2 hours. In November in Hopkinsville, expect temperatures between 58°F during the day and 38°F at night. Wrap up your sightseeing on the 26th (Fri) to allow time to drive to Paducah.

Things to do in Hopkinsville

Parks · Wildlife · Breweries & Distilleries · Historic Sites

Side Trips

Paducah

— 4 nights
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Discover out-of-the-way places like Purple Toad Winery and Paducah Riverwalk. Go for a jaunt from Paducah to Henderson to see Audubon State Park about 1h 45 min away. Next up on the itinerary: have fun and explore at River Discovery Center, admire the engineering at Kentucky Dam, steep yourself in history at Apple Valley Hillbilly Garden and Toyland, and walk around Bob Noble Park.

To find ratings, maps, reviews, and tourist information, use the Paducah road trip planner.

You can drive from Hopkinsville to Paducah in 1.5 hours. In November in Paducah, expect temperatures between 59°F during the day and 37°F at night. Finish your sightseeing early on the 30th (Tue) so you can fly back home.

Things to do in Paducah

Parks · Historic Sites · Wineries · Nature

Side Trips

Kentucky travel guide

4.5
Caves · Specialty Museums · Distilleries
The Bluegrass State
A diverse region of sprawling farmland and rich cultural heritage, Kentucky is the birthplace of American horse racing and home to the world-famous Kentucky Derby. While the cities of Lexington and Louisville experience the majority of the state's tourism, Kentucky is also a favorite among outdoor enthusiasts with its array of natural attractions, including the Cumberland Gap and the world's longest cave system at Mammoth Cave National Park. Take a tour through original Civil War battlefields to delve into the nation's history, or head to one of the many bourbon distilleries to learn more about Kentucky's most famous export.